Five New Tamarixetin Glycosides from Astragalus thracicus
Griseb. Including Some Substituted with the Rare
3-Hydroxy-3-methylglutaric Acid and Their Collagenase
Inhibitory Effects In Vitro

J 2024

Five New Tamarixetin Glycosides from Astragalus thracicus Griseb. Including Some Substituted with the Rare 3-Hydroxy-3-methylglutaric Acid and Their Collagenase Inhibitory Effects In Vitro

VASILEV, Hristo, Karel ŠMEJKAL, Sabína JUSKOVÁ, Jiří VÁCLAVÍK, Jakub TREML et. al.

Basic information

Original name

Five New Tamarixetin Glycosides from Astragalus thracicus Griseb. Including Some Substituted with the Rare 3-Hydroxy-3-methylglutaric Acid and Their Collagenase Inhibitory Effects In Vitro

Authors

VASILEV, Hristo (100 Bulgaria, belonging to the institution), Karel ŠMEJKAL (203 Czech Republic, belonging to the institution), Sabína JUSKOVÁ (703 Slovakia, belonging to the institution), Jiří VÁCLAVÍK (203 Czech Republic, belonging to the institution) and Jakub TREML (203 Czech Republic, belonging to the institution)

Edition

ACS Omega, WASHINGTON, American Chemical Society, 2024, 2470-1343

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10400 1.4 Chemical sciences

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 4.100 in 2022

Organization unit

Faculty of Pharmacy

DOI

http://dx.doi.org/10.1021/acsomega.3c09677

UT WoS

001200689200001

Keywords in English

FLAVONOL GLYCOSIDESANTIOXIDANTEXPRESSIONSAPONINSPARTS

Abstract

V originále

Along with the known kaempferol-3-O-alpha-l-rhamnopyranosyl-(1 -> 2)-[6-O-(3-hydroxy-3-methylglutaryl)]-beta-d-galactopyranoside (1), five new flavonoids, containing the rarely isolated aglycon tamarixetin, were isolated from a methanolic extract of the endemic Balkan species Astragalus thracicus Griseb. Three of the new compounds are substituted with 3-hydroxy-3-methylglutaryl residue (HMG), untypical for the genus Astragalus. The compounds were identified as tamarixetin-3-O-alpha-l-rhamnopyranosyl-(1 -> 2)-[6-O-(3-hydroxy-3-methylglutaryl)]-beta-d-galactopyranoside (2), tamarixetin-3-O-(2,6-di-O-alpha-l-rhamnopyranosyl)-beta-d-galactopyranoside (3), tamarixetin 3-O-beta-d-apiofuranosyl-(1 -> 2)-beta-d-galactopyranoside (4), tamarixetin-3-O-beta-d-apiofuranosyl-(1 -> 2)-[6-O-(3-hydroxy-3-methylglutaryl)]-beta-d-galactopyranoside (5), and tamarixetin-3-O-beta-d-apiofuranosyl-(1 -> 2)-[alpha-l-rhamnopyranosyl-(1 -> 6)]-beta-d-galactopyranoside (6). Selected compounds from A. thracicus were tested to evaluate their anticollagenase activity. The greatest effect was observed for quercetin-3-O-beta-d-apiofuranosyl-(1 -> 2)-beta-d-galactopyranoside, possibly due to the presence of an ortho-dihydroxy arrangement of flavonoid ring B. The effect on collagenase and elastase was further evaluated also by in silico study, and the test compounds showed some level of in silico interaction.

Citovat

VASILEV, Hristo, Karel ŠMEJKAL, Sabína JUSKOVÁ, Jiří VÁCLAVÍK and Jakub TREML. Five New Tamarixetin Glycosides from Astragalus thracicus Griseb. Including Some Substituted with the Rare 3-Hydroxy-3-methylglutaric Acid and Their Collagenase Inhibitory Effects In Vitro. ACS Omega. WASHINGTON: American Chemical Society, 2024, vol. 9, No 16, p. 18023-18031. ISSN 2470-1343. Available from: https://dx.doi.org/10.1021/acsomega.3c09677.

@article{2426464,
   author = {Vasilev, Hristo and Šmejkal, Karel and Jusková, Sabína and Václavík, Jiří and Treml, Jakub},
   article_location = {WASHINGTON},
   article_number = {16},
   doi = {http://dx.doi.org/10.1021/acsomega.3c09677},
   keywords = {FLAVONOL GLYCOSIDESANTIOXIDANTEXPRESSIONSAPONINSPARTS},
   language = {eng},
   issn = {2470-1343},
   journal = {ACS Omega},
   title = {Five New Tamarixetin Glycosides from Astragalus thracicus Griseb. Including Some Substituted with the Rare 3-Hydroxy-3-methylglutaric Acid and Their Collagenase Inhibitory Effects In Vitro},
   url = {https://pubs.acs.org/doi/10.1021/acsomega.3c09677},
   volume = {9},
   year = {2024}
}

TY  - JOUR
ID  - 2426464
AU  - Vasilev, Hristo - Šmejkal, Karel - Jusková, Sabína - Václavík, Jiří - Treml, Jakub
PY  - 2024
TI  - Five New Tamarixetin Glycosides from Astragalus thracicus Griseb. Including Some Substituted with the Rare 3-Hydroxy-3-methylglutaric Acid and Their Collagenase Inhibitory Effects In Vitro
JF  - ACS Omega
VL  - 9
IS  - 16
SP  - 18023-18031
EP  - 18023-18031
PB  - American Chemical Society
SN  - 24701343
KW  - FLAVONOL GLYCOSIDESANTIOXIDANTEXPRESSIONSAPONINSPARTS
UR  - https://pubs.acs.org/doi/10.1021/acsomega.3c09677
N2  - Along with the known kaempferol-3-O-alpha-l-rhamnopyranosyl-(1 -> 2)-[6-O-(3-hydroxy-3-methylglutaryl)]-beta-d-galactopyranoside (1), five new flavonoids, containing the rarely isolated aglycon tamarixetin, were isolated from a methanolic extract of the endemic Balkan species Astragalus thracicus Griseb. Three of the new compounds are substituted with 3-hydroxy-3-methylglutaryl residue (HMG), untypical for the genus Astragalus. The compounds were identified as tamarixetin-3-O-alpha-l-rhamnopyranosyl-(1 -> 2)-[6-O-(3-hydroxy-3-methylglutaryl)]-beta-d-galactopyranoside (2), tamarixetin-3-O-(2,6-di-O-alpha-l-rhamnopyranosyl)-beta-d-galactopyranoside (3), tamarixetin 3-O-beta-d-apiofuranosyl-(1 -> 2)-beta-d-galactopyranoside (4), tamarixetin-3-O-beta-d-apiofuranosyl-(1 -> 2)-[6-O-(3-hydroxy-3-methylglutaryl)]-beta-d-galactopyranoside (5), and tamarixetin-3-O-beta-d-apiofuranosyl-(1 -> 2)-[alpha-l-rhamnopyranosyl-(1 -> 6)]-beta-d-galactopyranoside (6). Selected compounds from A. thracicus were tested to evaluate their anticollagenase activity. The greatest effect was observed for quercetin-3-O-beta-d-apiofuranosyl-(1 -> 2)-beta-d-galactopyranoside, possibly due to the presence of an ortho-dihydroxy arrangement of flavonoid ring B. The effect on collagenase and elastase was further evaluated also by in silico study, and the test compounds showed some level of in silico interaction.
ER  -

VASILEV, Hristo, Karel ŠMEJKAL, Sabína JUSKOVÁ, Jiří VÁCLAVÍK and Jakub TREML. Five New Tamarixetin Glycosides from Astragalus thracicus Griseb. Including Some Substituted with the Rare 3-Hydroxy-3-methylglutaric Acid and Their Collagenase Inhibitory Effects In Vitro. \textit{ACS Omega}. WASHINGTON: American Chemical Society, 2024, vol.~9, No~16, p.~18023-18031. ISSN~2470-1343. Available from: https://dx.doi.org/10.1021/acsomega.3c09677.

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